Cesium carbonate → Ethyl 4-{4-[(dimethylamino)carbonyl]phenoxy}-2-ethyl-1-benzofuran-6-carboxylate

HRID 1643741ノート

反応式

HRID 1643741 の反応式
[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[C:8]([OH:17])[C:6]=2[CH:7]=1)[CH3:2].I[C:19]1[CH:29]=[CH:28][C:22]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>N1C=CC=CC=1.[Cu]I>[CH3:26][N:25]([CH3:27])[C:23]([C:22]1[CH:28]=[CH:29][C:19]([O:17][C:8]2[C:6]3[CH:7]=[C:3]([CH2:1][CH3:2])[O:4][C:5]=3[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=2)=[CH:20][CH:21]=1)=[O:24]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 8799334-iodo-N,N-dimethylbenzamideHCID 59560005Ethyl 2-ethyl-4-hydroxy-1-benzofuran-6-carboxylate

生成物 1

HCID 59560279Ethyl 4-{4-[(dimethylamino)carbonyl]phenoxy}-2-ethyl-1-benzofuran-6-carboxylate収率 31.8%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

A mixture of ethyl 2-ethyl-4-hydroxy-1-benzofuran-6-carboxylate (0.8 g, 3.4 mmol), 4-iodo-N,N-dimethylbenzamide (0.9 g, 3.3 mmol), Cs2CO3 (1.12 g, 3.4 mmol) and CuI (400 mg, 2.1 mmol) in pyridine (30 mL) was heated to 100° C. for 24 hours. TLC (petroleum ether/EtOAc 4:1) indicated the complete consumption of the phenol. The solvent was removed under reduced pressure. The residue was poured into water (20 mL) and extracted with EtOAc (30 mL×2). The combined organic layers were washed with brine (20 mL×2), dried over Na2SO4 and concentrated. The product was purified via silica gel column chromatography using petroleum ether/EtOAc (20:1 to 1:1) to afford the desired compound (400 mg, 30%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.97 (s, 1H), 7.56 (s, 1H), 7.43 (d, 2H), 7.00 (d, 2H), 6.27 (s, 1H), 4.44-4.35 (q, 2H), 3.15-3.04 (d, 6H), 2.83-2.78 (q, 2H), 1.45-1.37 (t, 3H), 1.37-1.26 (t, 3H).

後処理

  1. customthe complete consumption of the phenol
  2. customThe solvent was removed under reduced pressure
  3. additionThe residue was poured into water (20 mL)
  4. extractionextracted with EtOAc (30 mL×2)
  5. washThe combined organic layers were washed with brine (20 mL×2)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe product was purified via silica gel column chromatography

出典と根拠

ORDレコード
ord-059b22b447d44ba3aa3cdc0ec93dc56b
出典データセット
uspto-grants-2012_02
特許番号
US08119624B2

反応ノート

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